Some Kind of Beautiful (2014)

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Richard is a successful college professor who gives up a steady stream of one-night-stands and beautiful undergrads for fatherhood with much younger Kate. Three years later when Kate falls in love with someone else and moves out, she sends her sister, Olivia, to make sure Richard is properly caring for their son. Assuming Richard is back to his irresponsible playboy lifestyle, Olivia is shocked when she starts to fall in love with him herself.